Starting a business is hard. Running a company is harder. It’s often said it’s not the idea that matters — it’s the execution. I agree. But here’s the thing — you can’t possibly know how everything is going to take shape. You can’t know if your plans are going to go off without a hitch or if you’ll need to pivot.

Once an idea takes shape and turns into a product and that product turns into a company, it becomes something new. It no longer is your idea. It’s now about providing the maximum amount of value to the market you serve.

There will be unexpected bumps along your path. You’re going to be wrong. You’re going to have to take risks. And this all teaches us one fundamental truth: embarking on a startup venture is an exercise in embracing irregularities and learning from inevitable mistakes.

Here’s how you can brace yourself against these challenges and come out on top.

Lean on Your Trusted Advisors

Running a company is a maze of decisions, legal challenges, product updates, and management woes. Simply put, it can be exhausting to do it all alone. This is where your trusted advisors come into play. Whether you have a formal advisory board, a board of directors, close business allies or consultants to team up with, these guides are more than just a sounding board. They will help you steer your thinking, ask challenging questions, and provide guidance based on their expertise. Their wisdom and experience will guide you through.

Be Curious

In the early stages of your company, let curiosity guide you. Your hypothesis about what your market will find value in (and pay for!) is your North Star. This period is less about precision and more about exploration. It’s a time to test the waters, to see what resonates and what doesn’t. In some ways, your early adopters are not just customers; they are buying into your vision.

Build With Your Customer In Mind

Without a customer, you’re just a team trying to sell a product. It’s critically important to continuously communicate with your early adopters and ensure you’re giving them what they need. Maintain a consistent communication loop with your audience — this feedback is invaluable. The more you understand your customers, the better you can serve them.


As you embark on this journey, diversify your ideas and approaches to serving the market. This doesn’t mean losing focus but rather exploring different avenues to deliver on your core thesis and your vision. Each idea can provide insights into what your market truly needs and wants. It’s about finding that sweet spot where your passion meets the market’s needs.

Double Down on What Works

Once you find product/market fit, it’s time to double down. This stage is all about execution at a high level. Refine your product, make it better, more aligned with your customers’ needs. This is the phase where your initial hypotheses get validated, and your model gets fine-tuned.

Finding Mastery

We often give this advice: one product, one channel until you master it. It’s golden advice. Once you find market fit, focus on mastering it. This approach allows for a deep understanding of what you’re selling and to whom. Only when you have a firm grip on this should you consider diversification. It’s about building a strong foundation before expanding the empire.

Be Flexible

Lastly, don’t force what isn’t working. Entrepreneurship is as much about resilience as it is about adaptability. Go with what works and build from there. Sometimes, the market tells you something different from what you expected. Listen to it. Pivot if you must. Your agility in these moments can be the difference between success and failure.

Remember, the path to success is rarely linear. Embrace the irregularities, learn from your mistakes, and stay true to your vision. Looking to add to your roster of trusted advisors? We’d love to chat.

About the Author: Joe Schipani

Avatar photo
Joe Schipani is a Managing Partner at Cross/Section. Prior to founding Cross/Section, he had a successful career in leadership roles in sales, marketing, business development and operations. He focuses on growth, product, GTM strategy, and continuous improvement in front office functions.